rac-6-Hy-droxy-2,5,7,8-tetra-methyl-chroman-2-carboxamide from synchrotron data.

The crystal structure of the title water-soluble analogue of vitamin E, trolox amide, C(14)H(19)NO(3), solved and refined against synchrotron diffraction data, contains two mol-ecules in the asymmetric unit. In both molecules, the heterocyclic ring is in a half-chair conformation. The crystal packing features a herring-bone pattern generated by N-H⋯O hydrogen bonds between the hy-droxy and amide groups. O-H⋯O hydrogen bonds also occur.

Related literature

For background to the chemistry of trolox, its substituted amides and their applications as anti­oxidants and anti-inflamatory agents, see: Ross et al. (1995 ▶); Scott et al. (1974 ▶); Cort et al. (1975 ▶); Cohen et al. (1981 ▶); Walther et al. (1991 ▶); Silver et al. (1992 ▶); Netscher & Gautschi (1992 ▶); Van Ginkel et al. (1992) ▶; Moulin et al. (1998 ▶); Vajragupta et al. (2000 ▶); Koufaki et al. (2010 ▶). For the use of trolox as an inter­mediate for the synthesis of natural tocols such as vitamin E and α-tocotrienol, see: Cohen et al. (1979 ▶); Hyatt & Skelton (1997 ▶); Sakito & Suzokamo (1982 ▶); Sugai et al. (1991 ▶).

Experimental

Crystal data

C14H19NO3

M = 249.31

Monoclinic,

a = 9.11 (1) Å

b = 17.92 (2) Å

c = 15.95 (1) Å

β = 100.43 (1)°

V = 2561 (4) Å3

Z = 8

Synchrotron radiation

λ = 0.59040 Å

μ = 0.06 mm−1

T = 100 K

0.2 × 0.05 × 0.04 mm

Data collection

MAR315 CCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 2003 ▶) T min = 0.988, T max = 0.997

14016 measured reflections

6360 independent reflections

5153 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.147

S = 1.08

6360 reflections

327 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.25 e Å−3

Data collection: NECAT APS beamline software; cell refinement: HKL-2000 (Otwinowski & Minor, 1997 ▶); data reduction: HKL-2000; program(s) used to solve structure: SHELXD (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and pyMOL (DeLano, 2002 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002807/kp2304sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002807/kp2304Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H19NO3	F(000) = 1072
Mr = 249.31	Dx = 1.293 Mg m−3
Monoclinic, P21/c	Melting point: 492 K
Hall symbol: -P 2ybc	Synchrotron radiation, λ = 0.59040 Å
a = 9.11 (1) Å	Cell parameters from 6360 reflections
b = 17.92 (2) Å	θ = 1.4–23.5°
c = 15.95 (1) Å	µ = 0.06 mm−1
β = 100.43 (1)°	T = 100 K
V = 2561 (4) Å3	Needle, colourless
Z = 8	0.2 × 0.05 × 0.04 mm

MAR315 CCD diffractometer	6360 independent reflections
Radiation source: NECAT 24ID-C synchrotron beamline APS, USA	5153 reflections with I > 2σ(I)
Si111 double crystal	Rint = 0.030
ω scans	θmax = 23.5°, θmin = 1.4°
Absorption correction: multi-scan (SCALEPACK; Otwinowski et al., 2003)	h = 0→12
Tmin = 0.988, Tmax = 0.997	k = 0→24
14016 measured reflections	l = −21→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0846P)2 + 0.4358P] where P = (Fo2 + 2Fc2)/3
6360 reflections	(Δ/σ)max < 0.001
327 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. The crystal was mounted with vaseline on a pin attached capillary. Upon mounting, the crystal was quenched to 100 K in a nitrogen-gas stream supplied by an Oxford Cryo-Jet. Diffraction data were measured at the station 24-ID—C of the APS synchrotron by rotation method.

Geometry. All e.s.d.'s are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against all reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F.

	x	y	z	Uiso*/Ueq
O1	0.61019 (10)	0.45827 (5)	0.16067 (5)	0.0245 (2)
C2	0.47454 (14)	0.45990 (7)	0.19461 (8)	0.0237 (3)
C3	0.34104 (15)	0.47162 (7)	0.12365 (8)	0.0268 (3)
H3A	0.3515	0.5198	0.0950	0.032*
H3B	0.2487	0.4736	0.1481	0.032*
C4	0.32903 (14)	0.40842 (7)	0.05855 (8)	0.0247 (3)
H4A	0.2887	0.3633	0.0822	0.030*
H4B	0.2587	0.4231	0.0063	0.030*
C5	0.48962 (14)	0.34738 (7)	−0.03638 (8)	0.0231 (3)
C6	0.62994 (14)	0.33351 (7)	−0.05616 (8)	0.0235 (3)
C7	0.76145 (14)	0.36122 (7)	−0.00604 (8)	0.0232 (3)
C8	0.75096 (14)	0.40469 (7)	0.06572 (8)	0.0224 (2)
C9	0.61017 (14)	0.41713 (6)	0.08636 (7)	0.0215 (2)
C10	0.47925 (14)	0.39050 (7)	0.03598 (8)	0.0217 (2)
C11	0.45591 (14)	0.38690 (7)	0.24307 (8)	0.0233 (3)
O12	0.33708 (11)	0.37440 (5)	0.26791 (6)	0.0303 (2)
N13	0.57098 (13)	0.34076 (6)	0.25872 (7)	0.0271 (2)
H13A	0.5647	0.2995	0.2877	0.033*
H13B	0.6538	0.3514	0.2401	0.033*
C14	0.49388 (17)	0.52489 (7)	0.25803 (9)	0.0312 (3)
H14A	0.4095	0.5259	0.2884	0.047*
H14B	0.4975	0.5720	0.2272	0.047*
H14C	0.5870	0.5184	0.2991	0.047*
C15	0.35081 (15)	0.31770 (8)	−0.09261 (9)	0.0299 (3)
H15A	0.3000	0.3584	−0.1274	0.045*
H15B	0.2838	0.2968	−0.0570	0.045*
H15C	0.3784	0.2787	−0.1299	0.045*
O16	0.63187 (11)	0.29210 (6)	−0.12892 (6)	0.0325 (2)
H16A	0.7183	0.2925	−0.1404	0.049*
C17	0.91159 (15)	0.34490 (8)	−0.02946 (9)	0.0304 (3)
H17A	0.9123	0.2938	−0.0513	0.046*
H17B	0.9898	0.3502	0.0212	0.046*
H17C	0.9301	0.3801	−0.0734	0.046*
C18	0.88847 (15)	0.43836 (8)	0.12025 (9)	0.0302 (3)
H18A	0.8581	0.4729	0.1615	0.045*
H18B	0.9462	0.4654	0.0838	0.045*
H18C	0.9500	0.3985	0.1507	0.045*
O21	0.09463 (10)	0.20376 (5)	0.15518 (6)	0.0261 (2)
C22	−0.03768 (14)	0.18816 (7)	0.18944 (8)	0.0246 (3)
C23	−0.17485 (14)	0.19491 (8)	0.11915 (9)	0.0277 (3)
H23A	−0.1817	0.2464	0.0963	0.033*
H23B	−0.2658	0.1849	0.1431	0.033*
C24	−0.16637 (14)	0.13979 (8)	0.04698 (9)	0.0278 (3)
H24A	−0.2001	0.0901	0.0629	0.033*
H24B	−0.2350	0.1563	−0.0051	0.033*
C25	0.01411 (14)	0.09450 (7)	−0.04523 (8)	0.0242 (3)
C26	0.16025 (14)	0.08797 (7)	−0.06026 (8)	0.0244 (3)
C27	0.28233 (14)	0.11907 (7)	−0.00506 (8)	0.0236 (3)
C28	0.25737 (14)	0.15918 (7)	0.06677 (8)	0.0229 (3)
C29	0.11127 (14)	0.16416 (7)	0.08231 (8)	0.0228 (3)
C30	−0.01047 (14)	0.13307 (7)	0.02768 (8)	0.0235 (3)
C31	−0.04526 (15)	0.24820 (7)	0.25651 (8)	0.0270 (3)
O32	−0.15782 (11)	0.25283 (6)	0.28939 (6)	0.0353 (2)
N33	0.07066 (14)	0.29294 (7)	0.27773 (8)	0.0360 (3)
H33A	0.0696	0.3277	0.3166	0.043*
H33B	0.1490	0.2880	0.2530	0.043*
C34	−0.02493 (16)	0.11133 (7)	0.23290 (9)	0.0300 (3)
H34A	−0.1073	0.1049	0.2642	0.045*
H34B	0.0704	0.1079	0.2727	0.045*
H34C	−0.0298	0.0722	0.1896	0.045*
C35	−0.11451 (15)	0.06001 (8)	−0.10581 (8)	0.0291 (3)
H35A	−0.0827	0.0480	−0.1597	0.044*
H35B	−0.1979	0.0954	−0.1164	0.044*
H35C	−0.1465	0.0143	−0.0806	0.044*
O36	0.17961 (12)	0.04723 (6)	−0.13154 (6)	0.0315 (2)
H36A	0.2416	0.0691	−0.1561	0.047*
C37	0.43909 (15)	0.10894 (8)	−0.02105 (9)	0.0294 (3)
H37A	0.4698	0.1537	−0.0486	0.044*
H37B	0.4426	0.0657	−0.0582	0.044*
H37C	0.5069	0.1008	0.0333	0.044*
C38	0.38410 (14)	0.19683 (7)	0.12563 (8)	0.0268 (3)
H38A	0.4358	0.2309	0.0927	0.040*
H38B	0.4543	0.1590	0.1532	0.040*
H38C	0.3445	0.2250	0.1692	0.040*

	U11	U22	U33	U12	U13	U23
O1	0.0261 (5)	0.0241 (4)	0.0258 (4)	−0.0053 (3)	0.0114 (4)	−0.0031 (3)
C2	0.0277 (6)	0.0182 (5)	0.0282 (6)	0.0000 (5)	0.0130 (5)	−0.0012 (4)
C3	0.0281 (6)	0.0216 (6)	0.0326 (7)	0.0044 (5)	0.0104 (5)	0.0027 (5)
C4	0.0230 (6)	0.0242 (6)	0.0285 (6)	−0.0001 (5)	0.0091 (5)	0.0002 (5)
C5	0.0243 (6)	0.0203 (6)	0.0262 (6)	−0.0031 (5)	0.0083 (5)	0.0012 (5)
C6	0.0266 (6)	0.0203 (6)	0.0260 (6)	−0.0020 (5)	0.0112 (5)	−0.0013 (4)
C7	0.0231 (6)	0.0214 (6)	0.0273 (6)	−0.0016 (5)	0.0104 (5)	0.0033 (5)
C8	0.0231 (6)	0.0203 (6)	0.0255 (6)	−0.0023 (5)	0.0086 (5)	0.0040 (4)
C9	0.0256 (6)	0.0178 (5)	0.0232 (6)	−0.0030 (4)	0.0099 (5)	0.0010 (4)
C10	0.0225 (6)	0.0185 (5)	0.0261 (6)	−0.0015 (4)	0.0097 (5)	0.0025 (4)
C11	0.0280 (6)	0.0214 (6)	0.0225 (6)	−0.0009 (5)	0.0103 (5)	−0.0023 (4)
O12	0.0315 (5)	0.0293 (5)	0.0349 (5)	−0.0014 (4)	0.0189 (4)	0.0001 (4)
N13	0.0286 (6)	0.0229 (5)	0.0320 (6)	0.0012 (4)	0.0117 (5)	0.0041 (4)
C14	0.0400 (8)	0.0214 (6)	0.0349 (7)	−0.0012 (5)	0.0140 (6)	−0.0062 (5)
C15	0.0259 (7)	0.0327 (7)	0.0323 (7)	−0.0054 (5)	0.0087 (5)	−0.0049 (5)
O16	0.0290 (5)	0.0368 (5)	0.0349 (5)	−0.0045 (4)	0.0144 (4)	−0.0126 (4)
C17	0.0240 (6)	0.0363 (7)	0.0340 (7)	−0.0015 (5)	0.0136 (5)	−0.0005 (6)
C18	0.0252 (7)	0.0353 (7)	0.0309 (7)	−0.0073 (5)	0.0073 (5)	−0.0018 (5)
O21	0.0220 (4)	0.0269 (5)	0.0332 (5)	−0.0036 (3)	0.0152 (4)	−0.0040 (4)
C22	0.0223 (6)	0.0229 (6)	0.0322 (6)	0.0006 (5)	0.0144 (5)	0.0041 (5)
C23	0.0209 (6)	0.0299 (7)	0.0353 (7)	0.0029 (5)	0.0131 (5)	0.0063 (5)
C24	0.0193 (6)	0.0312 (7)	0.0342 (7)	−0.0012 (5)	0.0086 (5)	0.0048 (5)
C25	0.0245 (6)	0.0224 (6)	0.0269 (6)	−0.0027 (5)	0.0078 (5)	0.0066 (5)
C26	0.0284 (6)	0.0222 (6)	0.0250 (6)	−0.0023 (5)	0.0113 (5)	0.0034 (5)
C27	0.0226 (6)	0.0225 (6)	0.0285 (6)	−0.0011 (5)	0.0120 (5)	0.0043 (5)
C28	0.0214 (6)	0.0208 (6)	0.0286 (6)	−0.0011 (4)	0.0102 (5)	0.0036 (5)
C29	0.0226 (6)	0.0203 (6)	0.0279 (6)	0.0001 (4)	0.0112 (5)	0.0023 (4)
C30	0.0200 (6)	0.0226 (6)	0.0298 (6)	−0.0006 (4)	0.0098 (5)	0.0056 (5)
C31	0.0278 (7)	0.0237 (6)	0.0330 (7)	0.0047 (5)	0.0146 (5)	0.0040 (5)
O32	0.0342 (6)	0.0344 (5)	0.0434 (6)	0.0027 (4)	0.0238 (5)	0.0012 (4)
N33	0.0321 (6)	0.0329 (6)	0.0473 (7)	−0.0029 (5)	0.0189 (5)	−0.0144 (5)
C34	0.0332 (7)	0.0234 (6)	0.0342 (7)	−0.0021 (5)	0.0082 (6)	0.0041 (5)
C35	0.0282 (7)	0.0302 (7)	0.0292 (6)	−0.0047 (5)	0.0056 (5)	0.0049 (5)
O36	0.0366 (6)	0.0325 (5)	0.0296 (5)	−0.0084 (4)	0.0173 (4)	−0.0026 (4)
C37	0.0246 (6)	0.0331 (7)	0.0339 (7)	−0.0005 (5)	0.0143 (5)	−0.0004 (5)
C38	0.0224 (6)	0.0274 (6)	0.0326 (7)	−0.0026 (5)	0.0104 (5)	−0.0008 (5)

O1—C9	1.3958 (18)	O21—C29	1.3933 (18)
O1—C2	1.4364 (19)	O21—C22	1.4381 (18)
C2—C3	1.518 (2)	C22—C23	1.525 (2)
C2—C14	1.532 (2)	C22—C31	1.527 (2)
C2—C11	1.544 (2)	C22—C34	1.536 (2)
C3—C4	1.527 (2)	C23—C24	1.529 (2)
C3—H3A	0.9900	C23—H23A	0.9900
C3—H3B	0.9900	C23—H23B	0.9900
C4—C10	1.511 (2)	C24—C30	1.511 (2)
C4—H4A	0.9900	C24—H24A	0.9900
C4—H4B	0.9900	C24—H24B	0.9900
C5—C6	1.393 (2)	C25—C26	1.400 (2)
C5—C10	1.406 (2)	C25—C30	1.405 (2)
C5—C15	1.509 (2)	C25—C35	1.510 (2)
C6—O16	1.3803 (18)	C26—O36	1.3889 (18)
C6—C7	1.405 (2)	C26—C27	1.403 (2)
C7—C8	1.402 (2)	C27—C28	1.406 (2)
C7—C17	1.510 (2)	C27—C37	1.506 (2)
C8—C9	1.399 (2)	C28—C29	1.400 (2)
C8—C18	1.515 (2)	C28—C38	1.509 (2)
C9—C10	1.396 (2)	C29—C30	1.396 (2)
C11—O12	1.2387 (18)	C31—O32	1.2362 (18)
C11—N13	1.3230 (19)	C31—N33	1.320 (2)
N13—H13A	0.8800	N33—H33A	0.8800
N13—H13B	0.8800	N33—H33B	0.8800
C14—H14A	0.9800	C34—H34A	0.9800
C14—H14B	0.9800	C34—H34B	0.9800
C14—H14C	0.9800	C34—H34C	0.9800
C15—H15A	0.9800	C35—H35A	0.9800
C15—H15B	0.9800	C35—H35B	0.9800
C15—H15C	0.9800	C35—H35C	0.9800
O16—H16A	0.8400	O36—H36A	0.8400
C17—H17A	0.9800	C37—H37A	0.9800
C17—H17B	0.9800	C37—H37B	0.9800
C17—H17C	0.9800	C37—H37C	0.9800
C18—H18A	0.9800	C38—H38A	0.9800
C18—H18B	0.9800	C38—H38B	0.9800
C18—H18C	0.9800	C38—H38C	0.9800
C9—O1—C2	117.57 (9)	C29—O21—C22	116.31 (10)
O1—C2—C3	110.46 (12)	O21—C22—C23	109.68 (12)
O1—C2—C14	105.09 (11)	O21—C22—C31	106.05 (10)
C3—C2—C14	111.59 (11)	C23—C22—C31	108.91 (11)
O1—C2—C11	110.57 (10)	O21—C22—C34	110.22 (10)
C3—C2—C11	110.15 (11)	C23—C22—C34	112.81 (11)
C14—C2—C11	108.87 (12)	C31—C22—C34	108.94 (12)
C2—C3—C4	110.69 (11)	C22—C23—C24	110.84 (11)
C2—C3—H3A	109.5	C22—C23—H23A	109.5
C4—C3—H3A	109.5	C24—C23—H23A	109.5
C2—C3—H3B	109.5	C22—C23—H23B	109.5
C4—C3—H3B	109.5	C24—C23—H23B	109.5
H3A—C3—H3B	108.1	H23A—C23—H23B	108.1
C10—C4—C3	111.29 (11)	C30—C24—C23	112.47 (11)
C10—C4—H4A	109.4	C30—C24—H24A	109.1
C3—C4—H4A	109.4	C23—C24—H24A	109.1
C10—C4—H4B	109.4	C30—C24—H24B	109.1
C3—C4—H4B	109.4	C23—C24—H24B	109.1
H4A—C4—H4B	108.0	H24A—C24—H24B	107.8
C6—C5—C10	118.98 (11)	C26—C25—C30	118.81 (11)
C6—C5—C15	120.47 (12)	C26—C25—C35	120.54 (13)
C10—C5—C15	120.54 (12)	C30—C25—C35	120.64 (12)
O16—C6—C5	115.99 (11)	O36—C26—C25	116.73 (11)
O16—C6—C7	121.94 (12)	O36—C26—C27	121.25 (12)
C5—C6—C7	122.06 (13)	C25—C26—C27	121.99 (13)
C8—C7—C6	118.93 (12)	C28—C27—C26	119.20 (12)
C8—C7—C17	120.54 (11)	C28—C27—C37	119.85 (11)
C6—C7—C17	120.53 (13)	C26—C27—C37	120.93 (13)
C9—C8—C7	118.79 (11)	C29—C28—C27	118.43 (11)
C9—C8—C18	119.98 (12)	C29—C28—C38	120.41 (12)
C7—C8—C18	121.23 (12)	C27—C28—C38	121.16 (12)
O1—C9—C8	115.15 (11)	O21—C29—C30	121.98 (12)
O1—C9—C10	122.55 (11)	O21—C29—C28	115.50 (11)
C8—C9—C10	122.30 (12)	C30—C29—C28	122.50 (13)
C9—C10—C5	118.88 (12)	C29—C30—C25	119.02 (12)
C9—C10—C4	120.42 (12)	C29—C30—C24	120.70 (12)
C5—C10—C4	120.70 (11)	C25—C30—C24	120.28 (11)
O12—C11—N13	122.36 (13)	O32—C31—N33	122.47 (14)
O12—C11—C2	119.66 (11)	O32—C31—C22	119.38 (12)
N13—C11—C2	117.95 (12)	N33—C31—C22	118.15 (12)
C11—N13—H13A	120.0	C31—N33—H33A	120.0
C11—N13—H13B	120.0	C31—N33—H33B	120.0
H13A—N13—H13B	120.0	H33A—N33—H33B	120.0
C2—C14—H14A	109.5	C22—C34—H34A	109.5
C2—C14—H14B	109.5	C22—C34—H34B	109.5
H14A—C14—H14B	109.5	H34A—C34—H34B	109.5
C2—C14—H14C	109.5	C22—C34—H34C	109.5
H14A—C14—H14C	109.5	H34A—C34—H34C	109.5
H14B—C14—H14C	109.5	H34B—C34—H34C	109.5
C5—C15—H15A	109.5	C25—C35—H35A	109.5
C5—C15—H15B	109.5	C25—C35—H35B	109.5
H15A—C15—H15B	109.5	H35A—C35—H35B	109.5
C5—C15—H15C	109.5	C25—C35—H35C	109.5
H15A—C15—H15C	109.5	H35A—C35—H35C	109.5
H15B—C15—H15C	109.5	H35B—C35—H35C	109.5
C6—O16—H16A	109.5	C26—O36—H36A	109.5
C7—C17—H17A	109.5	C27—C37—H37A	109.5
C7—C17—H17B	109.5	C27—C37—H37B	109.5
H17A—C17—H17B	109.5	H37A—C37—H37B	109.5
C7—C17—H17C	109.5	C27—C37—H37C	109.5
H17A—C17—H17C	109.5	H37A—C37—H37C	109.5
H17B—C17—H17C	109.5	H37B—C37—H37C	109.5
C8—C18—H18A	109.5	C28—C38—H38A	109.5
C8—C18—H18B	109.5	C28—C38—H38B	109.5
H18A—C18—H18B	109.5	H38A—C38—H38B	109.5
C8—C18—H18C	109.5	C28—C38—H38C	109.5
H18A—C18—H18C	109.5	H38A—C38—H38C	109.5
H18B—C18—H18C	109.5	H38B—C38—H38C	109.5
C9—O1—C2—C3	−43.88 (14)	C29—O21—C22—C23	−51.64 (14)
C9—O1—C2—C14	−164.37 (10)	C29—O21—C22—C31	−169.10 (10)
C9—O1—C2—C11	78.31 (14)	C29—O21—C22—C34	73.14 (14)
O1—C2—C3—C4	60.30 (13)	O21—C22—C23—C24	59.96 (14)
C14—C2—C3—C4	176.82 (11)	C31—C22—C23—C24	175.62 (10)
C11—C2—C3—C4	−62.14 (14)	C34—C22—C23—C24	−63.30 (15)
C2—C3—C4—C10	−44.86 (15)	C22—C23—C24—C30	−39.37 (15)
C10—C5—C6—O16	−178.75 (10)	C30—C25—C26—O36	177.90 (11)
C15—C5—C6—O16	0.21 (17)	C35—C25—C26—O36	−1.46 (17)
C10—C5—C6—C7	0.03 (18)	C30—C25—C26—C27	−0.36 (18)
C15—C5—C6—C7	178.99 (11)	C35—C25—C26—C27	−179.72 (11)
O16—C6—C7—C8	178.19 (11)	O36—C26—C27—C28	−179.33 (11)
C5—C6—C7—C8	−0.53 (18)	C25—C26—C27—C28	−1.15 (18)
O16—C6—C7—C17	−1.37 (18)	O36—C26—C27—C37	−0.33 (18)
C5—C6—C7—C17	179.92 (12)	C25—C26—C27—C37	177.85 (12)
C6—C7—C8—C9	1.86 (17)	C26—C27—C28—C29	2.41 (17)
C17—C7—C8—C9	−178.58 (11)	C37—C27—C28—C29	−176.60 (11)
C6—C7—C8—C18	−177.76 (11)	C26—C27—C28—C38	−176.99 (11)
C17—C7—C8—C18	1.80 (18)	C37—C27—C28—C38	4.00 (18)
C2—O1—C9—C8	−167.53 (10)	C22—O21—C29—C30	22.81 (16)
C2—O1—C9—C10	12.70 (16)	C22—O21—C29—C28	−158.56 (11)
C7—C8—C9—O1	177.40 (10)	C27—C28—C29—O21	179.10 (10)
C18—C8—C9—O1	−2.97 (16)	C38—C28—C29—O21	−1.49 (17)
C7—C8—C9—C10	−2.83 (18)	C27—C28—C29—C30	−2.28 (18)
C18—C8—C9—C10	176.80 (11)	C38—C28—C29—C30	177.13 (11)
O1—C9—C10—C5	−177.91 (10)	O21—C29—C30—C25	179.31 (11)
C8—C9—C10—C5	2.34 (18)	C28—C29—C30—C25	0.78 (18)
O1—C9—C10—C4	2.66 (17)	O21—C29—C30—C24	−1.47 (18)
C8—C9—C10—C4	−177.10 (11)	C28—C29—C30—C24	179.99 (11)
C6—C5—C10—C9	−0.90 (17)	C26—C25—C30—C29	0.56 (18)
C15—C5—C10—C9	−179.86 (11)	C35—C25—C30—C29	179.91 (11)
C6—C5—C10—C4	178.53 (11)	C26—C25—C30—C24	−178.66 (11)
C15—C5—C10—C4	−0.43 (18)	C35—C25—C30—C24	0.69 (18)
C3—C4—C10—C9	14.64 (16)	C23—C24—C30—C29	11.06 (17)
C3—C4—C10—C5	−164.78 (11)	C23—C24—C30—C25	−169.73 (11)
O1—C2—C11—O12	−171.35 (11)	O21—C22—C31—O32	171.96 (11)
C3—C2—C11—O12	−48.97 (16)	C23—C22—C31—O32	53.99 (16)
C14—C2—C11—O12	73.68 (15)	C34—C22—C31—O32	−69.42 (15)
O1—C2—C11—N13	10.66 (15)	O21—C22—C31—N33	−8.72 (16)
C3—C2—C11—N13	133.04 (13)	C23—C22—C31—N33	−126.69 (14)
C14—C2—C11—N13	−104.31 (13)	C34—C22—C31—N33	109.89 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13A···O16i	0.88	2.13	2.971 (2)	160
N13—H13B···O32ii	0.88	2.49	2.896 (3)	109
O16—H16A···O32iii	0.84	1.91	2.631 (2)	143
N33—H33B···O12	0.88	2.29	2.861 (3)	123
N33—H33A···O36i	0.88	2.53	3.281 (3)	143
O36—H36A···O12iv	0.84	1.91	2.727 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N13—H13A⋯O16i	0.88	2.13	2.971 (2)	160
N13—H13B⋯O32ii	0.88	2.49	2.896 (3)	109
O16—H16A⋯O32iii	0.84	1.91	2.631 (2)	143
N33—H33B⋯O12	0.88	2.29	2.861 (3)	123
N33—H33A⋯O36i	0.88	2.53	3.281 (3)	143
O36—H36A⋯O12iv	0.84	1.91	2.727 (2)	165

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .